(±)-methyl 4-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (±)-methyl 4-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: methyl 4-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；methyl 4-(furan-2-yl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₁H₁₂N₂O₃S
• 分子量: 252.294
• InChiKey: RHPHIDDIYSRLDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  D-木糖 在 Fe₃O₄/SiO₂-SO₃H 作用下， 以 水 为溶剂， 反应 5.5h， 生成 (±)-methyl 4-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Dehydration of Xylose to Furfural and Its Valorization via Different Multicomponent Reactions Using Sulfonated Silica with Magnetic Properties as Recyclable Catalyst

  摘要：

  Sulfonated silica with magnetic properties was studied for dehydration of xylose to furfural and posteriorly for furfural valorization through the Biginelli and Hantzsch multicomponent reactions. Eleven polysubstituted heterocycles were obtained in excellent yields and without any side-product (81-91 %), using a multicomponent green methodology. The presence of Fe3O4 particles allows an easy separation from the reaction medium giving a high yield in the reusability studies.

  DOI：

  10.1007/s10562-014-1267-8

文献信息

• Microwave-Assisted and Iodine-Catalyzed Synthesis of Dihydropyrimidin-2-thiones via Biginelli Reaction Under Solvent-Free Conditions
  作者：Qingjian Liu、Ning Pan、Jiehua Xu、Wenwen Zhang、Fanpeng Kong

  DOI：10.1080/00397911.2011.593289

  日期：2013.1.1

  Abstract Microwave-assisted synthesis of 3,4-dihydropyrimidin-2-thiones via Biginelli reaction from aldehydes, acetoacetates, and thiourea in the presence of iodine under solvent-free conditions has been accomplished in good yields and purity without chromatographic separation. GRAPHICAL ABSTRACT

  摘要 在无溶剂条件下，在碘存在下，醛、乙酰乙酸酯和硫脲通过 Biginelli 反应合成 3,4-二氢嘧啶-2-硫酮，以良好的收率和纯度完成，无需色谱分离。图形概要
• B(C6F5)3 catalyzed one-pot three-component Biginelli reaction: An efficient and environmentally benign protocol for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
  作者：SANTOSH KUMAR PRAJAPTI、KESHAV KUMAR GUPTA、BATHINI NAGENDRA BABU

  DOI：10.1007/s12039-015-0867-1

  日期：2015.6

  procedure. Moreover, the applicability of the present methodology for large-scale synthesis of monastrol highlights its potential for bulk synthesis. Tris(pentafluorophenyl)borane catalyzed, one-pot, simple, efficient and environmentally benign protocol for the synthesis of dihydropyrimidinones/thiones via Biginelli reaction has been described.

  已经描述了通过Biginelli反应合成二氢嘧啶酮/硫酮的三（五氟苯基）硼烷催化的一锅法，简单，有效和环境友好的方案。本方案的主要亮点是催化剂用量低，毒性低，与酸不稳定的保护基团的相容性，反应时间短，始终如一的优异收率和简单的反应/后处理程序。而且，本方法学对大规模合成monastrol的适用性突出了其本体合成的潜力。 已经描述了通过Biginelli反应合成二氢嘧啶酮/硫酮的三（五氟苯基）硼烷催化的一锅法，简单，有效和环境友好的方案。
• Improving the Selectivity toward Three-Component Biginelli versus Hantzsch Reactions by Controlling the Catalyst Hydrophobic/Hydrophilic Surface Balance
  作者：Babak Karimi、Akbar Mobaraki、Hamid M. Mirzaei、Daryoush Zareyee、Hojatollah Vali

  DOI：10.1002/cctc.201300739

  日期：2014.1

  mesoporous solid acid catalysts, 3, which has a hydrophobic/hydrophobic balance in the nanospaces (mesochannels) in which the active sites are located, is found to be a significantly more selective catalytic system in the Biginelli reaction; it produces the corresponding 3,4‐dihydropyrimidin‐2‐one\thione (DHPM) 5 derivatives in good to excellent yields and excellent selectivities. Notably, in the case

  两种介孔固体酸SBA-15-PrSO 3 H 1，SBA-15-Ph-PrSO 3 H 2和基于周期性介孔有机硅（PMO）的固体酸Et-PMO-Me-PrSO的催化活性和选择性在无溶剂条件下，在醛，β-酮酸酯和尿素或硫脲的环境友好的单锅三组分Biginelli反应中比较了具有不同理化表面性质的3 H 3。在这些介孔固体酸催化剂中，3，在活性位点所在的纳米空间（介孔通道）中具有疏水/疏水平衡，在Biginelli反应中被发现是选择性更高的催化系统。它可以产生相应的3,4-二氢嘧啶-2-酮\硫酮（DHPM）5衍生物，产率高，选择性好。值得注意的是，在存在1的条件下进行苯甲醛，乙酸乙酰甲酯和尿素的三组分偶联反应时，会生成Hantzsch二氢吡啶4（≈37％）和Biginelli dihydropyrimidinone 5（≈49％）的混合物，而与2相同的反应（催化剂负载量也为1 MOl％）提供了
• Application of Design of Experiments (DoE) Approach for the Optimization of Phase-transfer Catalyzed Biginelli Dihydropyrimidinone (DHPM) Synthesis
  作者：T. Durai Ananda Kumar、N. Swathi、C.V.S. Subrahmanyam、K. Satyanarayana

  DOI：10.2174/1570178617999200812133809

  日期：2021.7

  Biginelli synthesis is more cumbersome and produces lower yields. Several improved methodsare reported in the literature to replace the Biginelli catalyst. The design of biocompatible organic transformation is a majorconcern and a versatile greener procedure to construct Biginelli analogues is in great demand.Factorial design guided, energy efficient and versatile synthesis of 3,4-dihydropyrimidin-2-(1H)-ones

  ：传统的 Biginelli 合成更麻烦，产量更低。文献中报道了几种改进的方法来替代 Biginelli 催化剂。生物相容性有机转化的设计是一个主要问题，并且非常需要构建 Biginelli 类似物的通用绿色程序。 3,4-二氢嘧啶-2-(1H)-酮 (DHPM) 的因子设计指导、节能和通用合成是发达。一次一个因素 (OFAT) 和析因设计 (23) 研究用于筛选自变量。通过研究确定潜在变量（苄基-n-三乙基氯化铵 (BTEAC) 和冰醋酸）的最佳水平. 析因设计 (32) 分析推断使用 BTEAC (10.25 mol%) 和冰醋酸 (7.6 ml) 是 60 分钟冷凝的最佳选择。使用优化的反应条件合成了 13 种新的 3,4-二氢嘧啶-2-(1H)-酮 (DHPM) 类似物。BTEAC的季铵离子稳定芳醛和烯化酮（乙酰乙酸烷基酯）中羰基的极化，通过N-酰基亚胺离子和迈克尔加合物的形成促进
• Ultrasound-Mediated Synthesis of 3,4-Dihydropyrimidin-2-(<i>1H</i>)-Ones (or Thiones) with NaHSO₄·H₂O
  作者：Karim Akbari Dilmaghani、Behzad Zeynizadeh、Maryam Amirpoor

  DOI：10.1080/10426507.2013.777725

  日期：2013.11.1

  A fast and efficient Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (or thiones) by the reaction of aromatic aldehydes, -dicarbonyls, and urea/thiourea using NaHSO4H2O/ultrasound system is presented. The reactions were carried out in refluxing n-hexane/CH3CN (2.5:0.5mL) to afford the products in excellent yields.